Diethyl Oxalate → Ethyl (3-methylphenyl)pyruvate

Reaction equation

F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9](=[O:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11].[CH3:16]C1C=C(C=CC=1)CBr.[Mg].C(OCC)(=O)C(OCC)=O>>[CH3:16][C:7]1[CH:2]=[C:3]([CH2:8][C:9](=[O:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:4]=[CH:5][CH:6]=1

Participants

Reactant 4

HCID 7268Diethyl Oxalate

HCID 12099m-Xylyl bromide

HCID 5462224Magnesium

HCID 18370709Ethyl (2-fluorophenyl)pyruvate

Product 1

HCID 18370163Ethyl (3-methylphenyl)pyruvateYield 72%

Procedure

The title compound was prepared as described for B4 using 3-methylbenzyl bromide (1.250 g, 6.75 mmol), magnesium (0.181 g, 7.43 mmol) and diethyl oxalate (1.974 g, 13.51 mmol). The resulting compound was isolated in the form of colorless oil in 72% yield and use instantly in next step.